AU726560B2 - Use of indole derivatives for the treatment of various diseases - Google Patents
Use of indole derivatives for the treatment of various diseases Download PDFInfo
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- AU726560B2 AU726560B2 AU43407/99A AU4340799A AU726560B2 AU 726560 B2 AU726560 B2 AU 726560B2 AU 43407/99 A AU43407/99 A AU 43407/99A AU 4340799 A AU4340799 A AU 4340799A AU 726560 B2 AU726560 B2 AU 726560B2
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Description
S F Ref: 372732DI
AUSTRALIA
PATENTS ACT 1990 COMPLETE SPECIFICATION FOR A STANDARD PATENT
ORIGINAL
Name and Address of Applicant: Actual Inventor(s): Address for Service: Pfizer Research and Development Company, N.V./S.A.
La Touche House International Financial Services Centre Dublin 1 REPUBLIC OF IRELAND Kathryn Louise Monkhouse, Paul Gupta, Shirley Jones, Juan Lahuerta, Gillian Christine Land, Susan Frances Robson, Gillian Mary Ryder Samuels, Alan Brian Wilson and Martin James Wythes Spruson Ferguson, Patent Attorneys Level 33 St Martins Tower, 31 Market Street Sydney, New South Wales, 2000, Australia Use of Indole Derivatives for the Treatment of Various Diseases Invention Title: The following statement is a full description of this invention, including the best method of performing it known to me/us:- 5845 New method of treatment This invention relates to new uses of certain indole derivatives in the treatment or prophylaxis of medical disorders.
International Patent Application WO 92/06973 discloses a series of indole derivatives which are potent serotonin (5-HT) agonists. These compounds are useful for treating disorders arising from deficient serotonergic neurotransmission comprising hypertension, depression, anxiety, eating disorders, obesity, drug 1C abuse, cluster headache, migraine, pain and chronic paroxysmal hemicrania and headache associated with vascular disorders. The compounds covered by WO *92/06973 include (R)-5-(methylaminosulphonylmethyl)-3-(N-methyipyrrolidin-2 ylmethyl)-1H-indole (Example 5A. known as CP-122.288) and (methylaminosulphonylmethyl)-3-(pyrrolidin-2-ylmethyl)-1H-indole (Example 6A.
5 known as CP-122.638).
It is known that CP-122.288 and CP-122.638 exhibit potency against neurogenic inflammation in dura mater [W.S Lee and M A Moskowitz. Brain Research 626 (1993). 303-305] It has now been found that compounds of formula I.
RI
R IHSO
H
wherein R' and R' independently represent H or alkyl. and their pharmaceutically acceptable salts, are useful in a considerable number of conditions These include dermatological disorders, such as psoriasis. eczema. atopic eczematous dermatitis; pruritis (also known as intractable itch) including itch asscciated with liver cirrhosis, cancer and haemodialysis. burns: scalds sunburn insect bites: 2 urticaria; and sweat gland abnormalities: bullous pemphigoid; photo-dermatoses; skin blisters; adult acne; chicken pox; and dermatitis herpetiformis; peripheral neuropathies including postherpetic neuralgia, diabetic neuropathies such as peripheral polyneuropathy and radiculopathy: causalgia and reflex sympathetic dystrophy; post-mastectomy neuralgia; post-surgical neuralgia and pain; vulvar vestibulitis; phantom limb pain; thalamic syndrome (central post-stroke pain); temporo mandibular joint syndrome; metatarsalgia (Morton's neuralgia); and neurogenic pain from nerve compression caused, for example, by a prolapsed intervertebral disc or carpal and tarsal tunnel syndromes; in arthritis, including osteoarthritis and rheumatoid arthritis; systemic lupus crythrematosus; fibromyalgia; ankylosing spondilitis; and tendinitis: gastrointestinal and urogenital diseases, including cystitis; gastroesophargeal reflux; gastritis; urge continence; inflammatory bowel disease; irritable bowel syndrome; the compounds are also effective in regulating gastrointestinal tract motility; i: headache associated with substances or their withdrawal drug withdrawal); tension headache; paediatric migraine; prophylaxis of migraine; and posttraumatic dysautonomic cephalgia; orofacial pain including toothache and pain of dental origin; earache; TMJ i pain (temporal mandibular joint pain); sinus pain; myofacial pain; non-arthritic and non- 20 musculoskeletal cervical pain; mouth ulcers; Meniere's disease; and atypical facial neuralgia.
allergic and chronic obstructive airways diseases including rhinitis; *conjunctivitis; bronchial oedema; bronchial asthma; neurological pulmonary oedema (adult respiratory disease syndrome); anaphylaxis; and angioedema; glaucoma (also known as intro-ocular pressure) and ocular inflammation.
As discussed below, a broad aspect of the present invention relates to a method of treatment or prophylaxis of any one of the above-mentioned conditions which comprises administering a therapeutically effective amount of a compound of formula I, as defined above, or a pharmaceutically acceptable salt thereof, to a patient in need of such o3 treatment.
Accordingly, a first aspect of the present invention provides a pharmaceutical composition comprising an effective amount of at least one compound of the formula \LIBaI02411 docaak R2
N
O
R O N
N
H
H
wherein R' and R 2 independently represent H or Ci-C alkyl, or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier, diluent or adjuvant therefor, characterised in that the composition is adapted for administration to the skin.
A second aspect of the present invention provides a method for the treatment or prophylaxis of dermatological disorders in a mammal requiring said treatment or :o prophylaxis, which method comprises administering to said mammal an effective amount of at least one compound of the formula 2 R 2
R
O
N
wherein R' and R 2 independently represent H or Ci-C 5 alkyl, or a pharmaceutically acceptable salt thereof, of a pharmaceutical composition containing said compound or of a pharmaceutical composition according to the first aspect of the present invention.
A third aspect of the present invention provides a method for the treatment or i. prophylaxis of arthritis in a mammal requiring said treatment or prophylaxis, which method comprises administering to said mammal an effective amount of at least one compound of the formula I, as defined above, or a pharmaceutically acceptable salt thereof, of a pharmaceutical composition containing such compound or of a pharmaceutical composition according to the first aspect of the present invention.
1 A fourth aspect of the present invention provides a method for the treatment or prophylaxis of gastrointestinal or urogenital diseases in a mammal requiring said treatment or prophylaxis, which method comprises administering to said mammal an effective amount of at least one compound of the formula I, as defined above, or a !l^armaceutically acceptable salt thereof, of a pharmaceutical composition containing [R \LIBa]0241 I doc'aak 2b such compound or of a pharmaceutical composition according to the first aspect of the present invention above.
A fifthi aspect of the present invention provides a method for the treatment or prophylaxis of allergic or chronic obstructive airways diseases in a mammal requiring said treatment or prophylaxis, which method comprises administering to said mammal an effective amount of at least one compound of the formula I, as defined above, or a pharmaceutically acceptable salt thereof, of a pharmaceutical composition containing such compound or of a pharmaceutical composition according to the first aspect of the present invention above.
I Another aspect of the invention relates to the use of a compound of formula I as ldetined above, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for use in any one of the above-mentioned conditions.
*0: *0 *.aa *C*a
C
*o* o I [R\LIBa]02411 doc aak Another aspect of the invention relates to a pharmaceutical formulation comprising a compound of formula I as defined above, or a pharmaceutically acceptable salt thereof, in admixture with a pharmaceutically acceptable adjuvant, diluent or carrier, characterized in that the formulation is adapted for administration to the skin. As mentioned below, conventional methods may be used to prepare the topical formulation.
The formulation may be adapted for administration to the skin to the exclusion of other routes of administration.
The compounds of formula 1, as defined above, may exist as optical isomers. The invention includes all optical isomers and mixtures thereof. However, compounds of I~ formula I having (R)-stereochemistry as shown in formula IA R2
N
R NHS02
N
However, it is preferred that R' and R each represent methyl. Compounds of formula I iC include CP-122.288, CP-122.638 and (R)-5-(aminosulphonylmethyl)-3-(Nmetlhylpyrrolidin-2-ylmethyl)-1H-indole.
'T
h e ac t i o n o f th e c o m poun d s of formula I in preventing or alleviating the conditions mentioned above is unexpected. Some of these conditions may be treated using capsaicin [(E)-N-[(4-hydroxy-3-methoxyphenyl)-methyl]-8-methyl-6-nonenamide] which is known to antagonise neurogenic inflammation by depicting IBa0241 oc:aak *R Ba]024 1 2doc:aa neuropeptide levels from neurones. However, the mode of action of capsaicin is totally different from that of the compounds of formula I When administered to a patient, capsaicin selectively activates primary sensory afferents to cause the release of substances known as "SP" (substance P) and "CGRP" (calcitonil gene relat d peptide) which cause inflammation The continued action of capsalcin results in the depletion of neuropeptides from the primary sensory afferents, so that these nerves lose their capacity to promote tissue inflammation Thus, the initial action of capsaicir is generally to cause intense itching and other effects associated with neurogenic inflammation. In contrast, the compounds of formula
I
o1 above suppress inflammation immediately by activating an inhibitory receptor located at the sensory nerve ending. Given this difference in function, the effects of the compounds of formula I cannot be predicted from the known effects of capsaicin: furthermore. they do not have the undesirable effects caused by the initial inflammation experienced when capsaicin in administered Pharmaceutically acceptable salts of the compounds of formula I include non-toxic :acid addition salts, that is salts containing pharmacologically acceptable anions Particular salts are mentioned in WO 92/06973. which also describes methods of p. reparing the compounds mentioned above and formulations containing the 20 compounds for administration to patients However, at least for oral administration, the fumarate salt is preferred.
4 The compounds of formula I and their salts defined above may be formulated in a conventional manner using one or more pharmaceutically acceptable carriers Thus the active compounds may be formulated for topical, oral. buccal intranasal parenteral intravenous, intramuscular or subcutaneous) or rectal administration. or in a form suitable for inhalation or insufflation Formulation methods are described in the above-mentioned Patent Application WO 92/06973 The daily dose of the compound administered to a patient for treatment of the above-mentioned conditions will be determined by a physician for any given patient but in general it will be typically 0.1 2 00mg of active ingredient per unit oral, parenteral or buccal dose which could be administered, for example, 1 to 4 times daily for an adult weighing 70kg). In an aerosol formulation each metered dose or "puff' may contain from 20pg to 1000g of the compound and the overall daily dose will be from 100pg to 10mg. However, it has been found that compounds CP-122.288 and CP-122,638 and (R)-5-(aminosulphonylmethyl)-3-(Nmethylpyrrolidin-2-ylmethyl)-1H-indole are active at doses several orders of magnitude less. The typical unit dose for topical, oral, buccal, intranasal, parenteral intravenous, intramuscular or subcutaneous), rectal, inhalation or insufflation administration will then be 1 nanogram 200mg for these compounds with a correspondingly reduced dose for aerosol formulations.
The following tests are believed to give an indication of a test compound's efficacy in the majority of the conditions mentioned above: 15 The effect of compounds of the invention in suppressing inflammation may be demonstrated by the method of Escott and Brain (Br J Pharmacol. (1993).
110. 772-776) in which oedema in the rat hind paw is measured after saphenous e ea nerve stimulation. The test compound is administered intravenously at different amounts and the results are recorded as the ratio of plasma extravasation in the S 2C stimulated/unstimulated hind paw. It is found that compound CP 122.288 has a f significant effect at administered amounts as low as 2 x 10'" mol/kg [Kajekar. Br J. Pharmacol. (1995), 115, 1-2].
(ii) The effect of a compound of the invention in suppressing vasodilation may be demonstrated by the method of Kajekar et al [Br. J Pharmacol. (1995), 115.
8Pj in which vasodilation in the rat hind paw is measured after saphenous nerve stimulation. The test compound is administered intravenously at different doses and the results are recorded as the change in the increase in skin blood flow It is found that CP-122.288 has a significant effect at doses as low as 2x10 2 mol/kg.
The invention is illustrated by the following examples Example 1 Topical aaueous -cream formnulation Ing lent Quantity (g) I Ingredient Quantity (9) (R)-5-(methylaminosulphonylmethyI)-3- 0.001 g (N-methylpyrrolidin-2-ylmethyl)-1 Hindole fumnarate Aqueous Cream BP 99 9 .999g 1kg of Aqueous Cream BP contains emulsifying ointment (300g), phenoxyethanol s (10g) and purified water (690g). 1kg of emulsifying ointment contains emulsifying wax (300g), white soft paraffin (500g) and liquid paraffin (200g).
0 *0 *5 9.
*5*0 Example2 Togical oily cream formulation Ingredient I Quantity (g) (R)-5-(methylaminosulphonylmethyl)-3- 0.001 g (N-methylpyrrolidin-2-ylmethyl)-1 Hindole fumarate Oily Cream BP 999.999g 1kg of Oily Cream BP contains wool alcohols ointment (500g), phenoxyethanol dried magnesium sulphate (5g) and purified water (485g). 1kg of wool alcohols ointment contains wool alcohols (60g), hard paraffin (240g). white soft paraffin (100g) and liquid paraffin (600g).
Claims (30)
1. A pharmaceutical composition comprising an effective amount of at least one compound of the formula R 0, 0 .0 a. wherein R' and R 2 independently represent H or C 1 -C 5 alkyl, or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier, diluent or adjuvant therefor, characterised in that the composition is adapted for administration to the skin.
2. A composition as defined in claim I wherein R 1 and R 2 each represent methyl.
3. A composition as defined in claim 1 or claim 2, wherein said compound is in the form of a fumarate salt.
4. A composition as defined in any one of claims 1 to 3, wherein the compound has the (R)-stereochemistry: N R A pharmaceutical composition comprising an effective amount of at least one compound of the formula R 2 N 0 H N [R:\LIBa]02411 .doc.aak 8 wherein R' and R 2 independently represent H or Ci-C 5 alkyl, or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier, diluent or adjuvant therefor, characterised in that the composition is adapted for administration to the skin, substantially as hereinbefore described with reference to any one of the examples.
6. A method for the treatment or prophylaxis of dermatological disorders in a mammal requiring said treatment or prophylaxis, which method comprises administering to said mammal an effective amount of at least one compound of the formula R 2 N O R S a N R N'' *H N H 1 0 wherein R 1 and R 2 independently represent H or CI-C 5 alkyl, or a pharmaceutically acceptable salt thereof, of a pharmaceutical composition containing said compound or of a pharmaceutical composition as defined in any one of claims 1 to
7. The method according to claim 6 wherein the dermatological disorders are S selected from the group consisting of eczema, atopic eczematous dermatitis, pruritis I .5 including itch associated with liver cirrhosis, cancer and haemodialysis, bums, scalds, sunburn, insect bites, urticaria, sweat gland abnormalities, bullous pemphigoid, photo-dermatoses, skin blisters, adult acne, chicken pox, and dermatitis herpetiformis.
8. A method for the treatment or prophylaxis of arthritis in a mammal requiring said treatment or prophylaxis, which method comprises administering to said mammal an effective amount of at least one compound of the formula I, as defined in claim 6, or a pharmaceutically acceptable salt thereof, of a pharmaceutical composition containing such compound or of a pharmaceutical composition as defined in any one of claims 1 to
9. The method according to claim 8 wherein the arthritic disorders are selected from the group consisting of oesteoarthritis and rheumatoid arthritis, systemic lupus erythrematosus, fibromyalgia, ankylosing spondilitis, and tendinitis. A method for the treatment or prophylaxis of gastrointestinal or urogenital diseases in a mammal requiring said treatment or prophylaxis, which method comprises 4-_s administering to said mammal an effective amount of at least one compound of the [R.\L1Ba]02411 doc:aak 9 formula 1, as defined in claim 6, or a pharmaceutically acceptable salt thereof, of a pharmaceutical composition containing such compound or of a pharmaceutical composition as defined in any one of claims 1 to S1. The method according to claim 10, wherein said gastrointestinal or urogenital disease is selected from the group consisting of cystitis, gastroesophargeal reflux, gastritis. urge continence, inflammatory bowel disease, irritable bowel syndrome, and regulating gastrointestinal tract motility.
12. A method for the treatment or prophylaxis of allergic or chronic obstructive airways diseases in a mammal requiring said treatment or prophylaxis, which method i0 comprises administering to said mammal an effective amount of at least one compound of the formula 1, as defined in claim 6, or a pharmaceutically acceptable salt thereof, of a pharmaceutical composition containing such compound or of a pharmaceutical composition as defined in any one of claims 1 to
13. The method according to claim 12, wherein said allergic or chronic 5 obstructive airways disease is selected from the group consisting of rhinitis, conjunctivitis, bronchial oedema, bronchial asthma, neurological pulmonary oedema, oo anaphylaxis and angioedema.
14. The method as claimed in any one of claims 6 to 13 wherein R' and R 2 each represent methyl. Oo.o 20 15. The method as claimed in any one of claims 6 to 13 wherein the compound of formula 1 is in the form of its fumarate salt.
16. The method as claimed in claim 6, wherein the medicament is for the treatment of pruritis. 1 7. The method as claimed in any one of claims 6 to 13 wherein the compound of formula I has the (R)-stereochemistry as shown in formula IA: R 2 N <3 IA R 1 NHSO 2 N H 1 8. Use of a compound of formula I, as defined in claim 6, in the manufacture of Sa medicament for the treatment of dermatological disorders. 0 t [RKLIBa]0241 I docaak
19. Use according to in claim 18 wherein the dermatological disorders are selected from the group Consisting of eczema, atopic eczematos dermatitis, pruritis including itch associated with liver cirrhosis, cancer and haemodialysis, burns, scalds, sunburn, insect bites, urticaria, sweat gland abnormalities, bullous pemphigoid, photo- dermatoses, skin blisters, adult acne, chicken pox, and dermatitis hcrpetiforiis. 0e, pox, and dermatitis herpetiformis. Use of a compound of formula as defined in claim 6, or a harmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment or prophylaxis of arthritis.
21. Use according to claim 20 wherein the arthritic disorders are selected from the Sconsisting of oesteoarthritis and rheumatoid arthritis, systemic lupus rythrematosus, fibromyalgia, ankylosing spondilitis, and tendinitis.
22. Use of a compound of formula I, as defined in claim 6, or a harmaceutically acceptable salt thereof, in the manufacture of a medicaiment for the treatmet of I. gastrointestinal or urogenital diseases. S
23. Use according to claim 22, wherein said gastrointestinal or urogeita disease groupa ontgogenital disease is selected from the group consisting of cystitis, gastroesophargeal reflux, gastritis, urge inenc iflammatry bowel disease, irritable bowel syndrome and regulaing gastrointestinal tract motility.
24. Use of a compound of formula I, as defined in claim 6, or a pharmaceutically 20 acceptable salt thereof, in the manufacture of a medicament for the treatment of allergic or chronic obstructive airways diseases.
25. Use according to claim 24, wherein said allergic or chronic obstructive airways disease is selected from the group consisting of rhinitis, conjunctivitis bronchial oedema, bronchial asthma, neurological pulmonary oedema, anaphylaxis and 2 angioedema.
26. The use as claimed in any one of claims 18 to 25 wherein R' and R 2 each represent methyl.
27. The use as claimed in any one of claims 18 to 25 wherein the compound of formula I is in the form of its fumarate salt. of0
28. The use as claimed in claim 18, wherein the medicament is for the treatment of pruritis. [R\LIBa]024 1 doc:aak 11
29. The use as claimed in any of claims 18 to 25 wherein the compound of lormula I has the (R)-stereochemistry as shown in formula IA: R 2 N 1IA R'NHSO 2 N H A compound of formula I R 2 \N O i 0 H wherein R' and R 2 independently represent H or C-C alkyl, or a harmaceutically l i-3 a yl, or a pharmaceutically acceptable salt thereof, when used for the treatment or prophylaxis of dermatological disorders in a mammal requiring said treatment or prophylaxis.
31. The compound of formula I when used, according to claim 30, wherein said 0 dermatological disorders are selected from the group consisting of eczema, atopic eczcmatous dermatitis, pruritis including itch associated with liver cirrhosis, cancer and haemodialysis, burns, scalds, sunburn, insect bites, urticaria, sweat gland abnormalities, bullous pemphigoid, photo-dermatoses, skin blisters, adult acne, chicken pox, and dermatitis herpetiformis.
32. A compound of formula I R 2 N O 1 N SO O HN H Swherein R' and R 2 independently represent H or CI-Cs alkyl, or a pharmaceutically 6 acceptable salt thereof, when used for the treatment or prophylaxis of arthritis in a SL mammal requiring said treatment or prophylaxis. [R\LIBa]0241 .doc:aak 12
33. The compound of formula I when used according to claim 32, wherein the arthritic disorders are selected from the group consisting of ocsteoarthritis and rheumatoid arthritis, systemic lupus erythrematosus, fibromyalgia ankylosng spondilitis and tendinitis. gia, nkylosing spondilitis, and
34. A compound of formula I R2 N R O H N H H \vwherein R' and R 2 independently represent H or CI-C 5 alkyl, or a pharmaceutically acceptable salt thereof, when used for the treatment or prophylaxis of gastrointestinal or urogenital diseases in a mammal requiring said treatment or prophylaxis.
35. The compound of formula I when used according to claim 34 wherein said gastrointestinal or urogenital disease is selected from the group consistig of cystitis Sastroesophargeal reflux, gastritis, urge continence, inflammatory bowel disease, irritable bowel syndrome, and regulating gastrointestinal tract motility.
36. A compound of formula I R 2 R 2 N* 1\ HN H wherein R' and R 2 independently represent H or CI-Cs alkyl, or a pharmaceutically acceptable salt thereof, when used for the treatment or prophylaxis of allergic or chronic obstructive airway diseases in a mammal requiring said treatment or prophylaxis.
37. The compound of formula I when used according to claim 36 wherein said allergic or chronic obstructive airways disease is selected from the group consisting of rhinitis, conjunctivitis, bronchial oedema, bronchial asthma, neurological pulmonary oedema, anaphylaxis and angioedema. [R.LIBa]0241 doc:aak 13
38. The compound of formula I when used according to any one of claims 30 to 37 wherein R' and R each represent methyl. S39. The compound of formula I when used according to any one of claims 30 to 37 wherein the compound of formula I is in the form of its fumarate salt. The compound of formula I when used according to claim 30 for the treatment of pruritis. Dated 11 September, 2000 Pfizer Research and Development Company, N.V./S.A. Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON *oo oo** *em oo *o• [R.LIBa]0241 1.doc.aak
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU43407/99A AU726560B2 (en) | 1994-10-12 | 1999-08-05 | Use of indole derivatives for the treatment of various diseases |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9420529 | 1994-10-12 | ||
| AU36997/95A AU3699795A (en) | 1994-10-12 | 1995-10-05 | Use of indole derivatives for the treatment of dermatological disorders peripheral neuropathied, arthritis, headache, orofacial pain, allergic or chronic obstructive airways disease, glaucoma and ocular inflammation |
| AU43407/99A AU726560B2 (en) | 1994-10-12 | 1999-08-05 | Use of indole derivatives for the treatment of various diseases |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU36997/95A Division AU3699795A (en) | 1994-10-12 | 1995-10-05 | Use of indole derivatives for the treatment of dermatological disorders peripheral neuropathied, arthritis, headache, orofacial pain, allergic or chronic obstructive airways disease, glaucoma and ocular inflammation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4340799A AU4340799A (en) | 1999-09-30 |
| AU726560B2 true AU726560B2 (en) | 2000-11-09 |
Family
ID=3724155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU43407/99A Ceased AU726560B2 (en) | 1994-10-12 | 1999-08-05 | Use of indole derivatives for the treatment of various diseases |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU726560B2 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992006973A1 (en) * | 1990-10-15 | 1992-04-30 | Pfizer Inc. | Indole derivatives |
| US5348968A (en) * | 1993-02-02 | 1994-09-20 | Adir Et Compagnie | Indole, indazole and benzisoxazole compounds |
-
1999
- 1999-08-05 AU AU43407/99A patent/AU726560B2/en not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992006973A1 (en) * | 1990-10-15 | 1992-04-30 | Pfizer Inc. | Indole derivatives |
| US5348968A (en) * | 1993-02-02 | 1994-09-20 | Adir Et Compagnie | Indole, indazole and benzisoxazole compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4340799A (en) | 1999-09-30 |
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